Cesium carbonate → HCID 131727231, compound

HRID 2375977Notes

Reaction equation

HRID 2375977 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH:5]([SH:7])[CH3:6])C.Br[CH2:10][C:11]1[CH:12]=[C:13]([CH:33]=[CH:34][CH:35]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([C:20]2[C:25]3[O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:24]=3[CH:23]=[CH:22][CH:21]=2)[CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)C>[CH3:1][O:3][C:4](=[O:8])[CH:5]([S:7][CH2:10][C:11]1[CH:12]=[C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([C:20]3[C:25]4[O:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:24]=4[CH:23]=[CH:22][CH:21]=3)[CH:19]=2)[CH:33]=[CH:34][CH:35]=1)[CH3:6]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 519709Ethyl 2-mercaptopropionateHCID 58657592HCID 58657592, compound

Product 1

HCID 131727231HCID 131727231, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl-2-mercaptopropionate (31 mg, 0.29 mmol) was added to a stirred suspension of 4-(3′-bromomethyl-biphen-3-yl)-dibenzofuran (100 mg, 0.24 mmol) and cesium carbonate (198 mg, 0.6 mmol) in 5 ml DMF. diluted with diethyl ether (30 mL) and washed with water (2×) and brine (3×). The ethereal solution was dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 30% ethyl acetate in hexane as eluent, afforded the title compound; methyl-2-(3′-dibenzofuran-4-yl-biphen-3-ylmethylsulfanyl)-propionate, as a colorless oil (105 mg, 94).

Workup

  1. washwashed with water (2×) and brine (3×)
  2. dry with materialThe ethereal solution was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the product by flash column chromatography

Sources & evidence

ORD record
ord-f117bccf04404736af4aa53f1d42af85
Source dataset
uspto-grants-2008_12
Patent number
US07465825B2

Reaction notes

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